Photographic silver halide emulsion containing color coupler



.fects, several remedies have already been proposed. Thus, colorcouplers which by the introgroups to render them diffusion-fast ingelatine Patented Feb. 6, 1 951 1;; j

UNITED stares PATENT oFFIce PnoroGRAr'Hio SILVER HALIDE EMUL- SIONCONTAINING COLOR COUPLER Philibert Leopold Jozef Raymond Merckx,Mortsol-Antwerp, Belgium, assignor to Gevaert- Photo-Producten N. V.,Mortsel-Antwerp, Belgium, a company of Belgium No Drawing: ApplicationMarch 14-, 1947, Serial Nor-734,852; In Germany September 22, 1943Section 1, Public'Law '690, August 8, 1946 Patentexpires September 22,1963 6 Claims. ('01. 956) I This invention relates to color photographyCH2CH2-, wherein one or more hydrogen materials and particularly tocolor photography atoms may be substituted as; for example: materialscontaining diifusion fast color couplers and dyestuffs and to methodsfor making color photography images. 5

The dyestuffs and color couplers incorporated c in multi-layer materialforcolor photography generally tend to pass from their proper layer intothe adjacent layers, that is, to diffuse. Con- I C: sequently, colordistortion and unsharpness of the images arise. In order to preventthese deduction of prescribed groups acquire substantive v propertiestothe binder have been suggested.

Furthermore, it is known to introduce into the dyestuffs or into thecolor couplers certain as, for example, aliphatic carbon chains of moredroxyanil has alsobeen proposed;

" amino derivatives of N-containing -heterocyclic wherein R has the samesignificance as above/Q Furthermore, the hydrogen atoms of the benzolring in the isatin nucleus may be replaced by any desired substituents.

For the preparation of the new diffusion-fast yestuffs or colorcouplers, a compound of the than five carbon atoms, hydroaromatic orhydrogenated heterocyclic radicals, sterine groups, carbohydrate groups,polypeptide groups, resin groups and groups of high polymeric compounds.'It is also known to use as diffusion-fast color couplers dyestufis suchas indigo dyestuffs or d their leuco derivatives substituted by aradical which contains a coupling function and which general formula(NH2 C6H4 X (X d1" can be split oil in a later treatment. Together orquadnvalent atom or atom groupmg; 71:2 3

or 4), for example, p-p'-diaminodiphenylsuch compounds. 'm methane orD-p'-diaminodiphenylene oxide is caused to react in the known way withchloral hydrate and hydroxylamine hydrochloride diluted hydrochloricsolution and in the presence f g g ggg are known as Q couplers f rsodium sulphate. The n fold isoni-troso" ue New I have found thatdyestuffs fi' if '35 iiti lfeiipitii ia fi totf fiiolfiiafii couplersare infusion-fast in gel-Ewing if they ice whereby the correspondingn-fold is'atin'is contain in their molecule a polyisatin group ofcad-(Or 8 th C 11 V 1 321) the following general formula pro u yn O T gv dyestufis or couplers of the invention-are ob'-- tained by thecondensation of these polyisatins 4 with 1-, 2-, 3- or fir-molecules ofa suitable compound containing an amido or hydrazine group.

Finally, cyano-, acylor carbalko y-acetyl 'I he condensation takes placereadily in the presence of sodium acetate (Miihlau und Ritter, R J. pr.Chem. (2), 73, p. 469).

The condensation of a compound containing a wherein R and R=H, alkyl,aryl, aralkyl, X=a hydrazine o p h the p y sa e may be of; div l t t orat m grouping c as Q' fected in the same manner as the condensation v ofa hydrazine with various ketones described in CH2', O-CH2CH2O, Berichte27 (1894), 688; 40 (1907), 712; and 41 CH2OCH2' (1908), 643.

lected from the group consisting of CN, acyl and carbalkoxy.

6. A photographic element comprising at least one light-sensitive silverhalide emulsion layer containing a color coupler fast to diffusion which5 corresponds to the following general formula wherein R and R representa member selected from the group consisting of hydrogen, alkyl,

aryl and aralkyl, X represents a divalent atom grouping, and Y and Yrepresent CN.

PIHLIBERT LEOPOLD JOZE'F RAYMOND MERCKX.

REFERENCES CITED The following refere file of this patent:

nces are of record in the UNITED STATES PATENTS Number Name 2,249,541Schinzel 2,334,495 Kendall Date July 15, 1941 Nov. 16, 1943

3. A PHOTOGRAPHIC ELEMENT COMPRISING AT LEAST ONE LIGHT-SENSITIVE SILVERHALIDE EMULSION LAYER CONTAINING A COLOR COUPLER FAST TO DIFFUSION WHICHCORRESPONDS TO THE FOLLOWING GENERAL FORMULA